AI in Your Business: Where to Start Workshop

Your company already has an operating system.

In two sessions, you’ll write it down.

WHAT?

Live workshop

Two working sessions

WHEN?

Tuesdays & Thursdays
11am UK

WHO?

Max 12 founders

No observers, no spectators

Not templates. A first-version OS built from your own business context, challenged by eleven other founders doing the same work in parallel.

Tim Barker built his AI company operating system at Attain IP and presented it at BoS Europe 2026. The reaction from a room full of founders who’d heard every AI pitch going: “someone actually doing it.” That talk created this workshop. In two sessions, you’ll see exactly how it gets built, then build a first version for yours.

Want to discuss fit before registering? Email mark@businessofsoftware.org


WHAT TO EXPECT

Two sessions. One OS.

Started live, not handed over.

Session 01 – TUESDAY

See how a company OS gets built

Surface the rules, constraints, and decision boundaries already living in your head. Document them roughly. The group critiques and sharpens.

Between sessions

Run the bootstrap on your own business

Run the AI bootstrap on your company. Review what it gets right and wrong. Write the correction list, the context your agent needs that no public source contains.

Session 02 – THURSDAY

Sharpen, correct, and map what’s next

Bring your correction list back to the group. Work out what your tools actually need from you, and whether the next step is building independently or joining the full four-week cohort.

The OS exists. Nobody has written it down yet.

Every company has an operating system. It’s in how decisions get made, how work flows, what the business will and won’t do, who has authority over what. Most of it has never been written down. It lives in your head, in your team’s habits, in institutional memory that walks out the door when people leave.

That was always a limitation. Now it’s the thing standing between you and any meaningful leverage from the tools everyone is talking about. Because those tools can only run well inside a system they can read. Every session starts from scratch. Nothing compounds. You’re still the one holding it together, because nothing else knows enough to.

You can see what this could be. That’s exactly what’s frustrating.

This workshop is the starting point. In two sessions across one week, you’ll see how a company OS gets built in practice, then build a first version for yours. Not a framework to think about later. A concrete start.

The BoS No Quibble Guarantee applies: if you attend and feel you didn’t get value, we will refund your workshop fee.

What You’ll Build

Not templates. A first-version OS built from your own business context, challenged by eleven other founders doing the same work in parallel.

Revised CLAUDE.md

The standing brief your tools read at the start of every session, written to reflect your actual values and constraints.

A Clear Path Forward

Whether that’s building independently or joining the full four-week cohort, you’ll leave knowing exactly what the right next step is.


Who This Is For

The cohort is capped at 12. Peer quality is part of what you’re paying for a room where almost every conversation is worth having.

This is for you if…


  • You’re a founder or CEO of a software business
  • You know there’s leverage here but haven’t yet found the right starting point
  • You want to know where a documented OS would change the quality of your decisions
  • You’re willing to do the prework and show up with your own business context

Probably not for you if…


  • You want a tour of tools or prompt engineering tips
  • You’re looking for generic productivity wins rather than a system that compounds
  • You want to watch without doing the hands-on work between sessions
  • You’re already tinkering regularly and hit a ceiling, the four-week cohort is the right next step

What you’ll need

The setup is straightforward.

  • Claude Desktop
    The interface you’ll use for all workshop sessions and prework.
  • Cowork mode (Claude Pro or Team plan)
    Required for the agent workflow used throughout the workshop.
  • Workshop skill suite (provided on enrolment)
    A set of skills tailored to the workshop workflow. You’ll receive access when you register.

If you’re not already using Claude in some capacity, this workshop isn’t the right starting point.


Who’s in the room

One facilitator, eleven peers, no audience.

Mark Littlewood
Founder, Business of Software

Mark has run Business of Software for 19 years, two annual conferences, more than 400 practitioner talks, and a community of founders building software companies that last. He has spent that time working out what actually separates the businesses that make it from those that don’t. This workshop is built on the same principle as every BoS event: helping entrepreneurs build better businesses alongside other smart people.

Registration open now

Your company already has an operating system. In two sessions, you’ll write it down.

Registration is open now. The cohort fills to 12 and closes.
Every Tuesdays & Thursdays · 11am UK · 2 hours each · Both sessions in one week
Max 12 participants · Workshop skill suite provided on enrolment

$500 per participant

The BoS No Quibble Guarantee: if you attend and feel you didn’t get value, we will refund your fee. No questions asked.  Questions about fit? Email Mark.

Common questions

What tools do I need before Session 1? Claude Desktop and a Claude Pro or Team plan (required for Cowork mode). The workshop skill suite is provided on enrolment, so no additional setup is needed before your first session. If you hit any issues, email mark@businessofsoftware.org before the session.

How is this different from the four-week cohort? The four-week cohort is for founders already using Claude and Cowork mode who want to build a complete governing system: strategy documents, a fully specified agent, and a first mission. It requires roughly 24–30 hours of work and produces a complete Agent OS. This workshop is the step before that. In two sessions you’ll have a bootstrapped start and a clear direction. If you leave ready to build that properly, the full cohort is the natural next step.

What’s the between-session work? Between sessions (roughly 1.5–2.5 hours) you run the AI bootstrap on your own company, review what it gets right and wrong, and write a correction list, the context your agent needs that no public source contains. Session 2 is built around what you bring from that work.